| Bisoctrizole |
 |
| IUPAC name | 2,2′-methanediylbis[6-(2H-benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol] |
| Identifiers |
| CAS number | 103597-45-1  Y |
| PubChem | 3571576 |
| SMILES | n1c6ccccc6nn1c2cc(cc(c2O)Cc5cc(cc(n3nc4ccccc4n3)c5O)C(C)(C)CC(C)(C)C)C(C)(C)CC(C)(C)C |
| InChI | 1/C41H50N6O2/c1-38(2,3)24-40(7,8)28-20-26(36(48)34(22-28)46-42-30-15-11-12-16-31(30)43-46)19-27-21-29(41(9,10)25-39(4,5)6)23-35(37(27)49)47-44-32-17-13-14-18-33(32)45-47/h11-18,20-23,48-49H,19,24-25H2,1-10H3 |
| InChI key | FQUNFJULCYSSOP-UHFFFAOYAP |
| ChemSpider ID | 2808671 |
| Properties |
| Molecular formula | C41H50N6O2 |
| Molar mass | 658.88 g/mol |
| Melting point | 195.7 °C |
 Y (what is this?) (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
Bisoctrizole (INN[1][2]/USAN[3], marketed by Ciba Specialty Chemicals as Tinosorb M, INCI methylene bis-benzotriazolyl tetramethylbutylphenol) is a benzotriazole based organic compound which is added to sunscreens to absorb UV rays.
Bisoctrizole is a broad spectrum ultraviolet radiation absorber, absorbing UVB as well as UVA rays. It also reflects and scatters UV. Bisoctrizole is a hybrid UV absorber, the only organic UV filter produced as microfine organic particles (< 200 nm),[4][5] like microfine zinc oxide and titanium dioxide. Where other organic UV absorbers need to be dissolved in either the oil or water phase, bisoctrizole dissolves poorly in both.
Bisoctrizole is added to the water phase of a sunscreen as a 50% suspension, while mineral micropigments are usually added to the oil phase. The bisoctrizole particles are stabilized by the surfactant decyl glucoside.
Bisoctrizole shows very little photodegradation and has a stabilizing effect on other UV absorbers, octyl methoxycinnamate (octinoxate) in particular.
When formulated into a sunscreen bisoctrizole has minimal skin penetration.[6] Unlike some other organic sunscreen actives, it shows no estrogenic effects in vitro.[7]
Bisoctrizole is not approved by the U.S. Food and Drug Administration (FDA), but is approved in the EU and other parts of the world.[8][9][10]
[edit] References
- ^ http://whqlibdoc.who.int/druginfo/18_4_2004_INN92.pdf
- ^ http://whqlibdoc.who.int/druginfo/INN_2005_list54.pdf
- ^ http://www.ama-assn.org/ama1/pub/upload/mm/365/bisoctrizol.doc
- ^ Ciba TINOSORB M
- ^ Blackwell Synergy - Int J Cosmet Sci, Volume 24 Issue 3 Page 170-185, June 2002 (Article Abstract)
- ^ Mavon A, Miquel C, Lejeune O, Payre B, Moretto P (2007). "In vitro percutaneous absorption and in vivo stratum corneum distribution of an organic and a mineral sunscreen". Skin Pharmacol Physiol 20(1): 10–20. doi:10.1159/000096167. PMID 17035717.
- ^ Ashby J, Tinwell H, Plautz J, Twomey K, Lefevre PA (December 2001). "Lack of binding to isolated estrogen or androgen receptors, and inactivity in the immature rat uterotrophic assay, of the ultraviolet sunscreen filters Tinosorb M-active and Tinosorb S". Regul Toxicol Pharmacol 34(3): 287–91. doi:10.1006/rtph.2001.1511. PMID 11754532.
- ^ Manage Account - Modern Medicine
- ^ CL1976L0768EN0150010.0001 1..107
- ^ Australian Regulatory Guidelines for OTC Medicines - Chapter 10
[edit] External links
| Sunscreening agents approved by the US FDA or other agencies | | | UVA: 400–315 nm • UVB: 315–290 nm • chemical agents unless otherwise noted | | | UVA filters | | | | UVB filters | | | | UVA+UVB filters | | | | | |
